Kinetically and thermodynamically controlled synthesis of 2,6-disubstituted cyclohexanone semicarbazones. A molecular mechanics study of a1,3-strai

Assumpta Castello, Carlos Jaime, Jorge Marquet, Marcial Moreno-Mañas

Research output: Contribution to journalArticleResearchpeer-review

13 Citations (Scopus)

Abstract

Reasonable values for Me-Me, H-Me and Me-H A1,3-strain have been evaluated by molecular mechanics calculations on differently substituted methylenecyclohexanes (5.46-6.75, 1.03 and 0.71 kcal mol, respectively). The chair-to-chair inversion barrier of methylenecyclohexanes has also been calculated. Methods are described for the thermodynamic and for the kinetic preparation of acylhydrazones of 2,6-dialkylcyclohexanones. A PMR analysis of the cis and trans-2,6-dimethylcyclohexanone semicarbazones has allowed the determination of the preferred conformers. The results agree with MM results on model hydrocarbons. Finally, a MM study of hydrocarbon models for the antibiotics isocycloheximide, cycloheximide and neocycloheximide points out to a decrease in stability on going from the former to the later, in agreement with the reported experimental results. © 1985.
Original languageEnglish
Pages (from-to)3791-3802
JournalTetrahedron
Volume41
Issue number18
DOIs
Publication statusPublished - 1 Jan 1985

Fingerprint Dive into the research topics of 'Kinetically and thermodynamically controlled synthesis of 2,6-disubstituted cyclohexanone semicarbazones. A molecular mechanics study of a<sup>1,3</sup>-strai'. Together they form a unique fingerprint.

  • Cite this